One of the main concerns of modern organizations is ethics, where only few institutions have not been affected by abuse of power. Recent history (e.g., Volkswagen emissions scandal, BP Deepwater Horizon oil spill, Wells Fargo account fraud, Theranos bankruptcy) highlights ethical breakdowns in organizations, which call organizational leaders to strive to behave responsibly, be an example for their followers, and to re-gain trust with them. The leaders’ behavior sets the stage for incorporating values into day-to-day operations in order to improve the relationship between leaders and followers. This project brings together various values-driven leadership approaches to managing organizations and offer leaders and managers strategies to mitigate ethical challenges. For inspiration, we look at the historical examples, such as moral leadership of the Benedictines, members of a religious order that has been founded in the sixth century. The Benedictines were able to establish their own businesses in various industries and successfully manage in the times of hardship. Using the example of Benedictine leadership, we explore how different leadership styles (ethical, servant, authentic leadership) can co-exist and complement each other in organizations that have been operating for more than 1,500 years. The results suggest that moral leadership of the Benedictines does include elements of ethical, authentic and servant leadership but goes beyond them by specifically delineating (religious) values that both leaders and followers adopt to develop trust relationships. Further, the Benedictines offer guidance for the selection of leaders, mentoring of followers, and finding meaning in work and entrepreneurial activities. Benedictine leadership also offers ideas how the implementation of religious values can help leaders and followers make decisions in morally challenging situations. These insights can be useful for leaders and entrepreneurs beyond the religious sector.